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They weren’t always the fastest or the most expensive. The sexiest or best designed or engineered. The most radical, iconic, famous, desired, or most outrageous. But they’re the coolest. It’s hard to define cool, but you know it when you see (or drive) it. As we kick off Motor Trend’s 60th Anniversary celebration, here’s a look-in random order-at 60 of the coolest, illist, chillist machines to roll earth’s highway during our watch, 1949-2009.

01. 1962-1969 AC SHELBY COBRA
If you could grab the $100 bill taped to the windshield of one owner’s when he floored his 427, you could keep the money. The owner never lost his Benjamin.

03. 1955-1963 MERCEDES-BENZ 300SL GULLWING
Before Jim Morrison, these were the Doors. The direct-injection Gullwing was the fastest, most advanced production automobile of its time.

04. 2002-2004 FERRARI ENZO
For the very rich, simply the V-12 supercar to crash. Of just 400 built, at least 14 have been destroyed and many more mangled spectacularly (see also YouTube: Eddie Griffin).

07. 1955-1957 CHEVROLET BEL AIR
Look up the word “Fifties” in the dictionary, and you’ll see picture of a Bel Air. (The scary, bloated thing in the other picture is the Creature from the Black Lagoon. Or Joe McCarthy.)

12. 1964 PONTIAC GTO
The first true musclecar. Promoted and nurtured by John DeLorean in the years before he began appearing on “The FBI’s Funniest Videos.”

13. 1961-1969 LINCOLN CONTINENTAL
It had suicide doors, carried JFK past the grassy knoll, and appeared on the TV series “Pushing Daisies.” Just a big ol’ funmobile. (Still one of the best-looking sedans ever, though.)

14. 1949 CADILLAC SERIES 62
Sporting a sensational new overhead-valve V-8, this was Motor Trend’s first-ever Car of the Year. Many subsequent COTY winners, ahem, are not on this list.

27. 1966-1970 OLDSMOBILE TORONADO
The first American front-drive automobile in three decades, with a Rocket V-8 motivating its missile-like bod.

28. 1953-1954 BUICK SKYLARK
To show the world who’s Big Cheese in design, GM released this limited-edition, largely handmade, ultra-pricey ($5000-plus) cabriolet. And the world did grin.

29. 1955-1965 CHRYSLER 300
At its debut, the most powerful production car in America (300 hp). The ’55 hit a record 127.580 mph on Daytona Beach; later 300 “letter cars” were even faster.

30. 1970 PLYMOUTH ROAD RUNNER SUPERBIRD/Dodge Charger DAYTONA
The wackiest thing with wings since “The Flying Nun.” Lured Richard Petty back to Plymouth, then earned the King a starring role in Pixar’s “Cars.”

40. 1961-1982 CHECKER MARATHON
Ask a New Yorker to draw a picture of an automobile, and he’ll draw a Marathon. (Also, it’ll be yellow and have an air freshener hanging from the rearview mirror.) Without it, Travis Bickle would still be in his room shouting, “You talkin’ to me?”

41. 1973-1974 LANCIA STRATOS HF
A wedge of cheesecake with a Ferrari V-6. We love cheesecake.

42. 1956-1959 BMW 507
Munich’s beautiful but poor-selling rival to the Gullwing almost drove the company into bankruptcy. Elvis gave away one of his to Ursula Andress.

43. 1953-1956 PORSCHE 550 SPYDER
After beating bigger, more powerful cars in road races, became known as “The Giant Killer.” Then “Giant” star James Dean died in one in 1955. We smell a conspiracy.

44. 1975-1981 MERCEDES-BENZ 6.9
Benz’s classic flagship sedan, with a hydropneumatic self-leveling suspension and more power than a Krispy Kreme salesman at a policemen’s ball.

45. 1951-1954 HUDSON HORNET
Fabulous? Won 27 of 34 NASCAR races in 1952 and 22 of 37 a year later. A half-century later returned as scene-stealer Doc Hudson in “Cars.”

46. 1964- PORSCHE 911
Any sports car with a production run of 45 years and counting must be doing something right. Not even “Romper Room” survived for so long.

47. 1969-1973 DATSUN 240Z
The most classic of all Japanese sports cars. For a while, “Z” even became a more popular letter than “X.”

48. 1949-1951 MERCURY
Foundation for countless “lead sleds,” the ’49 Merc has appeared in everything from “Rebel Without A Cause” to “Cobra.” Contrary to popular belief, however, it did not appear in “Sense and Sensibility.”

49. 1959-1967 JAGUAR MK II
Call it a “sedan” instead of a “saloon” and you’ll get warm beer thrown in your face.

50. 1976-2004 LOTUS ESPRIT
Giugiaro’s “folded paper” design was cool enough to land the Esprit in a couple James Bond flicks. The scene where the car converts into a submarine was proven to be every bit as authentic as Roger Moore’s ass-kicking skills.

58. 1960-1962 GHIA L6.4
Only 26 were built, but they got into the right hands-including those of Dean Martin and Frank Sinatra.

59. 1962-1964 FERRARI 250 GTO
Ranked #1 on Motor Trend Classic’s list of the Greatest Ferraris of All Time. “Using the engine to the fullest is like shooting down a steep waterslide.”

60. 1983-1984 Volkswagen Rabbit GTI
Those Euro-peeen drivers got the GTI several years earlier, but when the GTI hit the States in ’83, it virtually created the hot-hatch niche overnight. Best accessorized with a pair of Vuarnets.

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